Life on the Wild Side
by KritiPotterWhovian
Summary: Blair Waldorf decides to break free from her image that she has now. What happens when she find herself face to face with Chuck Bass, the guy known as the devil?
1. Chapter 1

Blair Waldorf sighed. She couldn't bear it any longer. Her life was a mess. When she had found out that her beloved father had been having a secret affair with a man, Blair had been in shock. But when her father had decided to leave his family and move to France with his male lover, Blair had had her fairy-tale life ripped apart. For all her life, she had ruled the Upper East Side, with her perfect life and her perfect parents. Everyone respected and admired her. But when her father was revealed to be gay, it caused a scandal. Blair didn't know what she would have done, if it wasn't for her best friend Serena van der Woodsen. Serena had been her support when Blair had wanted to hide in her room for the rest of her life. With the help of Serena, Blair had managed to gain control of her life once more and climb back up again.

But now, with her mother's news, Blair felt that her life was unravelling again. A couple of days ago, Eleanor Waldorf, Blair's mother had informed her that she had met someone and that he would be coming over for dinner. When Cyrus Rose had turned up, Blair had felt despair. Cyrus wasn't Cary Grant; he was more Danny DeVito. Having had to endure an awkwardly long family dinner with Cyrus chattering on as if he was already a part of the family, Blair had been shocked once more when her mother revealed to Blair that she was going to marry Cyrus.

Grabbing her phone, Blair dialled Serena's number.

"Serena, are you free? Mother announced that she's getting married to him. And he is unsuitable. He's five feet tall. He has a catchphrase. And he's a hugger. I was expecting Cary Grant and I got Danny DeVito!"

Blair listened to Serena as she replied.

"Yeah, can you come over? That would be great, thanks" Blair said before hanging up.

Hearing the ding of the elevator announcing someone's arrival, she called her maid.

"Who is it, Dorota?"

"It Miss Penelope and Miss Hazel for you"

Blair frowned. What did these two want? Blair got up to see what the problem was.

"What do you two want?" Blair asked when she got downstairs.

"Blair, we need to start planning the Fall Ball" Penelope replied, grabbing some folders from her bag.

"So we brought some ideas over" Hazel added. Blair scowled.

"I know what to do, I don't need you telling me" she snapped, snatching the folders from Penelope. Penelope smiled condescendingly.

"Now, go bother someone else" Blair gestured for them to leave. The two girls left. Dorota hovered behind Blair, pretending to tidy up while glancing at Blair subtly.

"What?" Blair glared at Dorota.

"Nothing" Dorota shook her head, hurrying off to find something else to do. Blair sighed, before heading up to her room again.

X

"Hey, B" Serena said as she waltzed into Blair's room. Blair stopped flicking through the magazine she was barely reading and sat up.

"Why is my life messed up? I swear it's like I'm being punished for all the bad things I did in my past life. Daddy left us for his male lover and now my mother is getting married to Danny DeVito's twin! Why me, Serena?"

"Blair, don't go there! Look, your life isn't a mess. If anyone's life is a mess, then it's my moms. She just got divorced from husband number three and has already found herself a new boyfriend. She's keeping him a secret for now, but it will be a short amount of time before he's husband number four" Serena said. Blair cracked a smile.

Serena's phone buzzed, and she checked it to see a new text.

"What is it?"

"Oh, just another party invite" Serena sighed, putting her phone away. Blair hesitated for a minute before speaking.

"What party is it?"

"Oh, it's the launch of Victrola"

Blair widened her eyes. Victrola was the starting point for Chuck Bass, the suave playboy son of Bart Bass. The whole week, the school had been talking about Victrola; everybody wanted to go, afterall everybody knew Chuck Bass. Blair jumped up.

"Serena, I have a great idea! Why don't we go to Victrola?"

"Are you sure, B? It's Chuck Bass territory. Everyone knows you're the queen of the Upper East Side, I mean, going into the devil's lair. I'm sure you've heard about parties hosted by Chuck" Serena frowned.

Blair stared at Serena.

"Serena, are you trying to change my mind? Come on, S, I need a break! I just want to get away from it all for one night, forget that I'm the queen who's supposed to be all perfect and have the perfect life when I don't!" Blair sighed. Serena stood up and walked over to Blair.

"Alright, Blair, we'll go. You're such a good drama queen, that's for sure" Serena rolled her eyes as Blair smiled.

"Thanks Serena! Now, which dress should I wear?"

X

Climbing out of the limo, Blair took in the sight before her. There were photographers all waiting to snap some photos of the high profile guests coming to the party. People with invites were allowed to enter the club immediately while those without, were queuing to get in. Behind her, Serena cleared her throat.

"You ready, B?! Serena asked, holding an invite in her hand.

"When am I never?" Blair replied turning back to Serena. The two girls grinned, grabbing each others arms before walking up to the red carpet towards the doorman.

"Serena, this way!"

"Blair Waldorf? Blair, can you look over here?"

The photographers called out, dying to get some pictures of the two girls. Blair and Serena giggled, waving, before rushing inside.

Once inside, Blair greedily took in Victrola.

"Oh my god" she heard Serena beside her. Blair felt the same. Victrola looked the epitome of classiness. While burlesque dancers performed on stage, guests were served by waitresses dressed in 1920s fashion. There was also a small casino held apart from the club.

"Well, who do we have here?" Carter Baizen walked up to the two. Carter was another person everyone knew. He and Chuck were of the same make, which meant the two being friends.

"Carter" Serena greeted him with a hug. Carter kept his eyes on Blair.

"Blair Waldorf, well that's one person who I didn't expect to see at a place like this"

"Then you clearly don't know me, Baizen"

"Blair and I are here to have a good time" Serena added, giving a look to Carter, who smirked in response.

"Well, can I get two beautiful ladies a drink?" Carter asked.

"I'll have a Gin Martini, and Serena?"

"I'll have the same"

Carter walked off to get the drinks.

X

An hour later, Blair was in the party mood, having had 5 drinks, She had last seen Serena laughing with Nate Archibald at the bar. Blair glanced at the burlesque dancers on the stage.

"They dance well, don't they?" someone spoke, coming to stand beside Blair. She kept her eyes on the dancers.

"I have moves better than them"

The person beside her scoffed in amusement.

"Then the stage is yours"

Blair looked at the person; it was Chuck Bass. She gulped in embarrassment while he smirked, reading the expression on her face. Chuck gestured to the stage; Blair hesitated before making her mind up. Blame the alcohol, she thought as she headed towards the stage.

Stepping onto the stage, Blair nodded her head at the dj to change the music. She turned her head to look at Chuck, and she saw Serena standing with him frowning. Listening to the music beat, Blair slowly let herself go; she began to move with the music. Smiling at Serena, Blair mouthed to her to come on stage. Serena started walking towards her.

"Blair, you're drunk! That's it, let's go home" Serena said as she met Blair on stage.

"No, what happened to having fun?" Blair pulled away from her.

"B, you'll thank me for this tomorrow" Serena started pulling Blair off stage.

"Hey, let the girl dance" someone shouted from the audience who had formed to watch Blair and Serena. Blair giggled. Serena finally managed to drag her off stage, to be met by Carter.

"Serena, why spoil the party? Blair seems to be having fun" he raised his eyes.

"Yes, Carter is right, I was having fun" Blair piped up.

"Carter, stay out of this! I know what your idea of fun is," Serena snapped at Carter before turning to Blair ", look Blair, just wait here while I get my stuff. Don't move!" Saying that, Serena walked off to get her stuff.

Carter glanced at Blair.

"How's the party?"

"It's great" Blair replied.

"We're moving onto the after party soon, you want to join us?"

"Count me in! If the party was great, then the after party is going to be twice as great"

"Chuck, I got Blair Waldorf here for the after party" Carter called out, looking behind Blair. She turned around to see Chuck walking towards them.

"Nice moves" Chuck complimented Blair. Blair smiled.

"Blair, you ready to go?" Serena appeared.

"Serena! We're going to the after party!" Blair grinned.

"No Blair" Serena shook her head.

"Come on Serena, Blair wants to go the after party. Let her" said Carter.

"No Carter, Blair's drunk and I need to get her home" Serena snapped, frowning.

"I'm not drunk" Blair exclaimed. Chuck decided to speak.

"Look Serena, why don't you come along with Blair? That way you can keep an eye on her. Blair has her fun, and then you take her home. I'll drop you off later. Trust me. Plus I heard Nathanial wanted to talk to you"

Serena stared at Chuck before sighing reluctantly.

"Fine! But you're definitely dropping us off, Chuck"

Blair cheered, hugging Serena.


	2. Chapter 2

Blair groaned as she opened her eyes. Her head was throbbing like there was no tomorrow. She closed her eyes again, willing her head to stop throbbing, to no avail.

"Dorota, bring me some aspirin" she croaked.

Frowning, she slowly sat up. Hearing her phone buzz, she picked it up.

_**Hey gorgeous!**_

She frowned.

_**Who is this? **_She texted back.

_**Not surprised you can't remember after last night. Carter**_

Blair widened her eyes in surprise, what was Carter Baizen doing texting her? And how had he got her number? And beyond that, what had happened last night? Blair tried to remember but all she got was blank.

_**Baizen? What are you doing texting me? How did you get my number? And more importantly, what happened last night?**_

_**Ha-ha! You gave me your number last night Blair. I didn't know you were such the party animal. You sure livened up the after party back at Chuck's place. **_

Blair groaned. What had she done last night? Her phone buzzed again. It was Serena.

_**Morning B. You ok?"**_

_**Serena, please tell me nothing happened between me and Carter Baizen yesterday!**_

_**Nothing happened, except a kiss. After that, I took you home, courtesy of Chuck, who gave us his limo"**_

Blair closed her eyes. She had kissed Carter Baizen. Wow, how drunk had she been? Remembering Carter she quickly texted him back.

_**Wow, I must have been really drunk last night to have kissed you**_

_**Ouch, you hurt my feelings. Though I do remember you were eager for more before Serena dragged you away**_

Blair frowned deeply.

_**I'm not that desperate Baizen. Getting mixed up with you is like getting mixed up with the devil. Now quit texting me, I plan to stay well clear from you.**_

Blair felt relieved when Carter stopped texting. Leaving her phone, she headed downstairs.

"Miss Blair, you're finally awake. It's late. Mrs Eleanor already go work" Dorota saw Blair.

"Dorota, quiet. I have a headache. Now bring me some aspirin"

Dorota walked off muttering before returning with a bottle.

"What's that, Dorota?" Blair asked curiously.

"It drink sent by a Mr Chuck Bass. He say it hangover remedy" Dorota handed the bottle to Blair.

"Ok" Blair was confused; Chuck Bass was sending her hangover remedies.

Curiously, she opened the bottle, sniffed the contents before drinking it. She felt a bit light headed.

"Dorota, did you get his number? I have to thank him for this"

"He say he save it on your phone already" Dorota replied. Blair nodded even though she was freaking out inside. She had got so drunk that she had now got Chuck Bass' number saved on her phone. Chuck Bass was the devil incarnate.

Slowly, she started to get brief flashbacks of the night before; she remembered going to the after party at Chuck's place, of her and Carter dancing, the kiss, then her laughing and giggling while Serena pulled her into a limo. Blair groaned in mortification; what had she done, never again was she getting that drunk.

Rushing back to her room, she quickly texted Serena.

_**I'm coming over to yours now. Be there in 15 minutes.**_

X

"Blair, hey, are you ok?" Serena greeted Blair as she marched into Serena's room. Blair frowned.

"No, Serena, why did you let me get that drunk last night? I kissed Carter Baizen! What was I thinking?"

"I tried to take you home after the show you put on at Victrola. But you wanted to go to the after party and I got overruled by Chuck and Carter"

"Never listen to me when I'm drunk, S!"

"Point noted for next time. Look, I'm sorry about yesterday. I should never have agreed to Chuck. Then we wouldn't have gone to the after party and you wouldn't be the talk of the town" Serena sighed. Blair froze.

"What?"

"Yeah, I'm sorry B, you are on the headlines of every gossip column" Serena mumbled, pushing Serena's laptop towards Blair.

Blair read what was on the screen. QUEEN B PARTIES WITH THE DEVIL. BLAIR WALDORF CUTTING LOOSE. WHO KNEW BLAIR WAS A PARTY ANIMAL? Blair groaned in despair.

"Mother is going to kill me!"

X

"Blair, can I have a word?" Eleanor Waldorf said as Blair walked out of the elevator. Blair sighed before following her mother.

"What is this?" Eleanor asked gesturing to some printed articles that were on the table in Eleanor's study.

"It's not what you think, mother"

"0h then please tell me what it is, Blair?"

Blair looked away. Eleanor sighed loudly before speaking again.

"Blair, as a Waldorf, you have an image. I just wish you would act according to that image. I mean, look at Serena, why can't you be like her?"

Eleanor dismissed her, and Blair headed straight for her room. Even though she was accustomed to her mother's disapproval, it still hurt even now. Blair longed for her mother's approval; just once she wished that her mother would commend her. So when she faced her mother's disappointment, she felt guilt for not acting to her mother's wishes.

Blair ruminated about what Eleanor had said about Serena. Obviously her mother liked Serena; to her Serena was the perfect daughter. Blair felt a stab of jealousy at this. No matter how much hard Blair tried to imitate Serena, Eleanor always found some fault in her. Suddenly, Blair's phone buzzed.

_**Hope that the hangover remedy I sent earlier worked CB. **_Blair knew instantly that it was Chuck.

_**Thank you for that. It worked.**_

_**I'm having a party at my place tonight. I'm hoping to see you.**_

Blair was set to replying that she wasn't interested and that last night was a one-off. But then she stopped herself; she thought of Eleanor. She already knew that her mother didn't approve of Blair's activities last night, so Blair didn't care. She experienced a wild feeling of rebellion; she wanted to go against her mother.

_**Are you inviting me?**_

_**Yes, if it wasn't obvious enough.**_

_**It wasn't but the answer is yes.**_

_**That's great. I'll have my limo pick you up at 8.**_

Blair gave a little smirk at the small flirtation that had just between her and Chuck. What was she doing? She was going to a party held by Chuck Bass! Normally Blair would have shuddered at this but tonight she just simply did not care. Her life was already going downhill anyway; she just wanted to forget some of her troubles for a while, forget how bad her life was turning out.

Thinking that, she headed to her wardrobe to choose a dress for the party.

**AN: Thanks to olimgossip and Sparkleyangel for reviewing. Thanks to Lula24, Nelson0987 and Shayyyy Love as well. I hope you guys like this chapter too. **


	3. Chapter 3

**AN: Thanks to Manhattonacmxoxo, IGetLostInWords, Sparkleyangel and Gihanti14 for reiewing. I hope you read and review this chapter too. And thanks to all those guest users who gave review too. **

Blair walked into the room. The party was in full spring. A group of drunk girls were dancing in the middle of the room, who were being admired by a group of lads. Blair spotted Chuck and Nate sitting at the bar.

"Waldorf" Chuck nodded in acknowledgement as she approached the two.

"Bass"

Nate stood up and gave Blair a hug.

"Hey Blair, what are you doing here? Where's Serena?" he said, looking around the room for the blonde.

"I was invited and Serena's not here. I came alone" Blair replied, taking a seat next to Nate.

"Oh" Nate nodded warily. Blair turned to look at a smirking Chuck.

"I didn't think you would actually come"

"I wouldn't normally, but I figured I need a change" Blair shrugged.

Chuck reached for a shot glass and filled it with vodka before passing it to Blair. She looked at him and Chuck nodded, challenging her to drink it. Blair grabbed the glass, quickly tipping her head back and swallowing. She grimaced as the drink quickly made its way down, leaving only its aftertaste.

"Now you're really making me doubt my impression of you. There I was thinking Blair Waldorf doesn't do shots" drawled Chuck.

"The old Blair didn't. But this Blair, who knows, she's different"

Nate interrupted, "Blair, are you sure about this? Maybe I should call Serena and tell her to come pick you up"

Blair turned to Nate, "Yes I'm sure Nate. No need to call Serena" Nate frowned, keeping silent.

Behind them, Carter Baizen spoke, "Well, if it isn't Blair Waldorf again, I thought you were staying away from us" Blair rolled her eyes.

"I changed my mind"

While she had been replying to both Nate and Carter, Chuck had again filled Blair's glass with vodka, passing it to her as a challenge. Blair took his challenge and she quickly finished the drink in one swallow. Behind her, Carter chuckled in amusement. Nate's frown increased and he slowly took out his face, without the three noticing.

"What's next, Bass?" Blair smirked at Chuck.

However, before Chuck could reply, Carter put his hand on Blair's arm. "I need to have a word with Blair for a minute".

Pulling Blair away from Chuck and Nate, Carter led her over to a corner, where they would be unseen.

"What is it, Carter?"

Carter retrieved something from his pocket. "Here, I got some for you". He handed her a small packet filled with white powder. Blair knew it wasn't sugar.

"Carter, what?" she began to question.

"You asked for some last night" he whispered, glancing around to see that no one had seen them.

"I did what?" Blair raised her eyes in surprise. "Look, I don't know what I did or say last night, but I'm never going to do this" she said, gesturing to the packet in her hand. Carter stared at her.

"You take it" Blair handed the packet back to Carter before walking away.

X

Back at the bar, Nate had wondered off, while Chuck had turned around, facing the room and was whispering something to a redhead. Blair poured herself another drink. Carter had followed her back, the packet back in his pocket.

"Ah, you're a Dom girl?" Carter nodded towards the bottle of Dom Perignon in Blair's hand. Chuck casually glanced towards Blair and Carter before standing up and leading the redhead off somewhere more private.

"Maybe" Blair shrugged. She sipped the drink and glanced around the room.

Carter smirked as he sat down on the seat Chuck had just vacated.

"You're a funny one, Waldorf?"

Blair turned to him in interest. Carter shook his head in amusement.

"There's this side of you that you show to the world and then there's another side to you when you're drunk. I saw that side of you last night and I have to say I'm intrigued by that side of you" he continued.

"Oh really, Baizen, then what's the other side of me?" teased Blair.

"You let go, you were more carefree, and you were also wilder than Serena" Carter added. Blair nodded, raising her eyes. They stared at each other; Carter leaning in towards Blair. For a moment they didn't move; then slowly Blair leaned in, her head moving towards Carter's. However before they kissed, they were interrupted by someone.

"Blair!" they turned to see Serena, with Nate behind her.

X

"Blair, what was that?" Serena asked, as Blair quickly stood up and walked away. Serena followed her to the balcony.

"Blair!" she called, turning Blair around to face her.

"Serena, hi, great party, isn't it?" Blair smiled, trying to change the conversation. Serena frowned.

"Oh, give me a break Serena, we didn't kiss, alright" Blair huffed.

"But you were about to! Come on, you tell me, if I hadn't come on time, then you would have kissed him," Serena exclaimed, "Carter, of all people, B you know Carter is bad news. I thought you had some standards"

"Who are you to talk about standards? You go out a lot with your socialite friends; get drunk till you can't stand and then shack up with the nearest guy around! At this rate, I'm surprised you haven't checked into rehab yet!" Blair snapped. Serena blinked in dismay.

"B-"

"I am sick and tired of all your crap Serena. You drift through life like you don't have any care in the world, while I'm stuck dealing with all your issues and I still get the raw deal. Everyone loves you, even my own mother. Even after trying to be the perfect daughter, she can't be bothered with me; it's only you, in everyone's eyes. So I am not sorry for trying to get a break, because I can't be your back-up forever"

Blair walked back in, with Serena slowly following. Carter and Nate approached them.

"Everything alright?" Carter asked, noticing Blair's stormy face and Serena's downcast face.

"Yes, Serena feels tired and she has to go home. Nate, why don't you walk her down?" Blair smiled stiffly.

"Yeah Nate, why don't you do just that? I need to talk to Blair again." Carter said, nodding to Nate.

Serena looked to Blair before walking away, quickly followed by Nate.

"So where were we?" Carter asked, turning to Blair.

X

Blair opened her eyes wearily. She stared at the white ceiling above her, feeling a sense of unusualness. Her bed seemed softer than usual and her silk comforter seemed to be missing. Blair also felt the absence of her pillow. She pulled her head up and looked around. Gasping, she realised, this wasn't her bedroom but Chuck Bass' lounge. She had fallen asleep in Chuck Bass' apartment. She quickly got up and heard sounds of someone making coffee. Behind her, Chuck was making himself coffee. He turned around and smiled, seeing Blair.

"You're awake"

"Yes" Blair answered awkwardly. What should she say next? She should apologise for sleeping over.

"Do me a favour. Wake Carter up for me, he's ruining the coffee table" Chuck said, nodding behind Blair. She turned to see Carter sleeping on the coffee table. Walking up to Carter, she shook him.

"Baizen, wake up" she hissed. Carter didn't move. She tried again with no result.

"Here, try this" Chuck walked over and poured a cup of water over Carter, who instantly jumped awake in shock.

"What the hell, Bass?!" Carter shouted.

"Get up, you're ruining the coffee table" Chuck just smirked. Carter frowned before noticing Blair standing there.

"Morning Blair" he stood up and walked up to her, sliding his arms around her waist. She smacked them away.

"What are you doing?"

"Nothing we weren't doing last night" Carter whispered. Chuck had gone back to the bar and was busy drinking his coffee.

Blair groaned.

"Look, I can't remember last night yet and I'm still tired and my head hurts like hell. So can we please keep this crap for later." Blair stated.

"Drink this" Chuck said, sliding a bottle apart from all the other bottles. Blair looked at it.

"No, I'm not drinking alcohol in the morning" She shook her head.

"It's hangover remedy. Remember the one I sent over yesterday" Chuck replied. Blair walked over and poured herself a mug. Carter left to get a change of clothes from his room two floors down.

"Thanks again for the remedy" Blair said, her head feeling a lot lighter after the drink. Chuck shrugged.

Blair turned to leave when the doors to the lift opened, and out walked Georgina Sparks.

"Well, look who it is, Blair Waldorf, and what is she doing in the devil's lair?"


End file.
